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3-({3-[(1S,4aS,6S,7S,9S,9aR)-1,6-dimethyl-2-oxodecahydro-6,9-epoxy-4a,7-methanobenzo[7]annulen-1-yl]propanoyl}amino)-2,4-dihydroxybenzoic acid

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Identification

Generic Name
3-({3-[(1S,4aS,6S,7S,9S,9aR)-1,6-dimethyl-2-oxodecahydro-6,9-epoxy-4a,7-methanobenzo[7]annulen-1-yl]propanoyl}amino)-2,4-dihydroxybenzoic acid
DrugBank Accession Number
DB08366
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 443.4896
Monoisotopic: 443.194402287
Chemical Formula
C24H29NO7
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 2Not AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylaminobenzoic acid and derivatives
Alternative Parents
Salicylic acids / Anilides / Benzoic acids / Benzoyl derivatives / Resorcinols / N-arylamides / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Oxepanes / Fatty amides
show 12 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acylaminobenzoic acid or derivatives / Anilide / Aromatic heteropolycyclic compound / Benzoic acid / Benzoyl / Carbonyl group / Carboxamide group / Carboxylic acid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XADCWKSMHQPTGH-OFBLZTNGSA-N
InChI
InChI=1S/C24H29NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-4,12,15,20,26,29H,5-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1
IUPAC Name
3-{3-[(1S,5S,6R,7S,9S,10S)-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridecan-5-yl]propanamido}-2,4-dihydroxybenzoic acid
SMILES
[H][C@]12C[C@]3([H])O[C@@]1(C)C[C@@]1(C2)CCC(=O)[C@@](C)(CCC(=O)NC2=C(O)C=CC(C(O)=O)=C2O)[C@]31[H]

References

General References
Not Available
PubChem Compound
16086836
PubChem Substance
99444837
ChemSpider
17245480
ZINC
ZINC000035050252
PDBe Ligand
P9A

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0144 mg/mLALOGPS
logP2.45ALOGPS
logP3.24Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.96Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area133.16 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity115.72 m3·mol-1Chemaxon
Polarizability44.69 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5661
Blood Brain Barrier-0.782
Caco-2 permeable-0.6954
P-glycoprotein substrateSubstrate0.7704
P-glycoprotein inhibitor INon-inhibitor0.9305
P-glycoprotein inhibitor IINon-inhibitor0.8106
Renal organic cation transporterNon-inhibitor0.9186
CYP450 2C9 substrateNon-substrate0.7226
CYP450 2D6 substrateNon-substrate0.812
CYP450 3A4 substrateSubstrate0.6913
CYP450 1A2 substrateNon-inhibitor0.8335
CYP450 2C9 inhibitorNon-inhibitor0.8514
CYP450 2D6 inhibitorNon-inhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8335
CYP450 3A4 inhibitorNon-inhibitor0.9476
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8182
Ames testNon AMES toxic0.6614
CarcinogenicityNon-carcinogens0.9485
BiodegradationNot ready biodegradable0.9897
Rat acute toxicity2.9926 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9709
hERG inhibition (predictor II)Non-inhibitor0.8182
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0010900000-3dcce75414121062146c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-0007900000-00bf9672e8e4ecb5ae0e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g6u-0692700000-14b085d88f947166b348
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001m-0958800000-97f5895a9a41022e707d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0981300000-aa6faffa6ce223e810b6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0419000000-5412094bb9dda6a3bc15
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.49486
predicted
DeepCCS 1.0 (2019)
[M+H]+194.8694
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.78194
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-oxoacyl-[acyl-carrier-protein] synthase 2
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Beta-ketoacyl-acyl-carrier-protein synthase ii activity
Specific Function
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Has a preference for short chain acid substrates and may function to...
Gene Name
fabF
Uniprot ID
P0AAI5
Uniprot Name
3-oxoacyl-[acyl-carrier-protein] synthase 2
Molecular Weight
43045.39 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52